tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

Base Information

Chemical Name:tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate
CAS No.:291517-50-5
Molecular Formula:C₂₇H₄₀N₂O₈
Molecular Weight:520.623
Hs Code.:

Synonyms:tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

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Chemical Property of tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

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Technology Process of tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

There total 7 articles about tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 29.0%

: tert-butyl (2S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl]prolinate

: 291517-50-5
tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

: 291517-51-6
tert-butyl (2S,3'R)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

Guidance literature:: With hydrogen; platinum on activated charcoal; In ethyl acetate; at 22 ℃; for 96h; under 2250.18 Torr;
DOI:10.1016/S0040-4020(00)00355-0

Reference yield:

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 291517-50-5
tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / LiBEt₃H / tetrahydrofuran / 3 h / -100 °C

2.1: NaH / tetrahydrofuran / 2 h / 22 °C

2.2: 82 percent / tetrahydrofuran / 24 h / 22 °C

3.1: 71 percent / LiBH₄ / diethyl ether / 22 °C

4.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 22 °C

5.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

5.2: 82 percent / CH₂Cl₂ / 1.5 h / -78 °C

6.1: 58 percent / H₂ / Pt/C / ethyl acetate / 96 h / 22 °C / 2250.18 Torr

With lithium borohydride; potassium tert-butylate; hydrogen; sodium hydride; lithium triethylborohydride; Dess-Martin periodane; platinum on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 1.1: Reduction / 2.1: Metallation / 2.2: Condensation / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation / 6.1: Catalytic hydrogenation;
DOI:10.1016/S0040-4020(00)00355-0

Reference yield:

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 291517-50-5
tert-butyl (2S,3'S)-trans-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)propyl]prolinate

Guidance literature:: Multi-step reaction with 2 steps

1.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

1.2: 82 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 58 percent / H₂ / Pt/C / ethyl acetate / 96 h / 22 °C / 2250.18 Torr

With potassium tert-butylate; hydrogen; platinum on activated charcoal; In dichloromethane; ethyl acetate; 1.1: Metallation / 1.2: Condensation / 2.1: Catalytic hydrogenation;
DOI:10.1016/S0040-4020(00)00355-0